Remember when newspapers debated the value and merits of using Twitter? Well, there’s a new question for news organizations to consider: Can newspapers use Twitter for advertising?

In the last few weeks, The Hartford Courant and The (New Orleans) Times-Picayune have experimented with using Twitter as a new advertising channel. At the Courant, they’ve started offering twice-daily deals to local businesses — think Groupon by tweet — to their followers. The Times-Picayune, more controversially, used Twitter to advertise itself — or at least its website, as the online division of its parent company, Advance Publications, paid New Orleans Saints players to tweet about the newspaper’s relaunched Saints site on Nola.com.

This isn’t exactly new territory, as a number of papers have experimented with droppings ads into Twitter in the last year. (Not to mention non-news outlets like, um, Kim Kardashian, for whom pay-per-tweet is a long-standing phenomenon.) Tweets offer another ad unit to sell, and when you’ve got an advertising salesforce in place, it almost — almost — seems like a no-brainer. And with the money floating around the paid-tweet world, it’s hard not to blame news organizations for wanting in on the market; five figures for tweeting endorsements is well within the reach of a popular reality TV star. Can Twitter advertising for newspapers work?

When I called up the Courant to talk about their sponsored tweet program, digital platform editor Rick Hancock told me “we don’t like to talk about our business plans and strategies” and declined to comment further.

From what I can tell the Courant runs their promotions twice a day, in an a.m. and p.m. tweet marked with SPONSORED and a link to the advertiser’s own site. On Oct. 25, they ran two sponsored tweets, one for a local Nutcracker production, another for a liposuction business (the “Official body sculpting company of the Miss Connecticut Organization”). Using Twitter search, it doesn’t look like the tweets got much traction aside from a few comments questioning the tweets. But since the tweets had photos attached, a check of Twitpic stats shows the Nutcracker ad got at least 120 views and liposuction ad 115. One thing worth noting: I haven’t seen any sponsored tweets from the Courant since.

In the case of the Times-Picayune, the product being hawked was neither liposuction or dancing dolls but the paper itself, namely the newly redesigned site for the paper’s coverage of the Super Bowl XLIV-winning New Orleans Saints. Advance Digital paid five Saints players to tweet promotional links to the site, which is more focused on community features than its predecessor. According to a Times-Picayune story about the campaign (and the confusion inside the paper about it — the newsroom didn’t know about the arrangement):

For instance, [Saints quarterback Drew] Brees’ nearly 700,000 Twitter followers received this message on Oct. 18: “Who Dats! If you didn’t join the NOLA Saints community this morning… join now!” The post included a link to the Saints page on NOLA.com and was retweeted, or forwarded, by 29 people.

The following day, prolific tweeter Vilma wrote: “I’ve been checking out the new #Saints community on NOLA. All my Who Dats need to join!” Vilma’s post was retweeted by 10 of his followers.

(It’s worth noting that Brees’ tweet and Vilma’s ended with the hashtag #spon, which some social media types are pushing as a semi-legible indicator of a sponsored tweet. A Twitter search for #spon is an enlightening look into what sorts of companies are paying people to tweet: at the moment, Verizon, Clorox, Pepperidge Farm, and Q-Tips.)

Here, it’s also unclear what sort of impact the Twitter promotion may have had. I emailed John Hassell, vice president of content for Advance Digital, to ask about any impact to traffic to Nola.com and have yet to hear back.

Though using Twitter as an advertising medium is still relatively new for news organizations, two outlets, MinnPost and the Austin American-Statesman, were early to experiment with the idea.

Since 2009, MinnPost has been running “real-time ads” on their site, which incorporate a business’ Twitter or RSS feed. Joel Kramer, CEO and editor of MinnPost, told me they’ve brought in about $30,000 through the ads, but that figure amounts to less than five percent of all advertising revenue. Kramer said most businesses are excited at the prospect of social media and the idea of real-time ads, but enthusiasm doesn’t always translate into sales. “I would say most people we show it to find it cool and interesting, but most are still struggling thinking about that kind of ad,” said Kramer.

Robert Quigley, the former social media editor for the Statesman, said he considers Twitter a promising advertising medium, but one that’s particularly tricky for newspapers to monetize. Quigley, who’s now a professor of journalism at the University of Texas, said the problem isn’t the ethical issues (though they exist) but more about the systems in place for newspaper advertising.

The Statesman’s plan called for clearly labeled sponsored tweets twice daily on their main Twitter account as well as their Austin360 feed. The ad staff secured the business and crafted the message, and once it got the okay from Quigley, it would go into the streams. Quigley trained and advised the advertising staff on social media, as well as how to pitch businesses on the platform, but he said his editor didn’t want to blur the newsroom/advertising divide too much. “Our editor, rightly, was concerned about me getting too close to the advertising side,” he said. “He didn’t want me meddling too much around in advertising. I was a newsroom employee, a journalist, and that wall between the two crumbled a little bit.”

Even if you get past the ethical issue, there’s little incentive for advertising staffs to sell sponsored tweets. If CPMs for online ads are a drop in the bucket compared to rates for print ads, the cost of a sponsored tweet (reportedly $300 a day for the Statesman) is not going to make anyone forget department store inserts as a revenue source. Unsurprisingly, some advertisers still prefer an old school system even though sponsored tweets could offer improved metrics for evaluating ads through Bitly or other analytical tools. “It’s not a tried and true method,” he said. “Retailers love having statistics and the kind of results they’ve counted on for years.”

Maybe it’ll just take time for businesses to warm up to the idea of advertising through the newspaper on Twitter. But the platform poses another problem: Newspapers are trying to insert themselves as a middleman in a medium that doesn’t require one. Joe’s Pizza has the same ability to publish on Twitter as the local daily does, and the audience monopoly that once existed in print is exploded on a democratized medium like Twitter. Sure, that local daily likely has more followers than Joe’s — but maybe not, and that pizza joint has other routes to reaching Twitter users than buying space in the daily’s stream. Twitter provides a new audience, but it also provides a channel for businesses to take matters into their own hands.

Still, even an incremental amount of new revenue is still new revenue. But news organizations still have a lot of work to do to figure out how best to integrate ads and Twitter. “It hasn’t been completely figured out yet,” Quigley said. “Maybe there is no figuring it out. Perhaps advertising in the Twitter stream is something that won’t work very well.”